Toluene → HCID 13335302, compound

HRID 1981573Notes

Reaction equation

HRID 1981573 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][CH2:11][CH3:12])=[CH:4][C:3]=1[N:13]=[C:14]=[O:15].C1(C)C=CC=CC=1.C[O:24][C:25]([NH:27][NH2:28])=O>C1C=CC=CC=1>[Cl:8][C:6]1[C:5]([O:9][CH2:10][CH2:11][CH3:12])=[CH:4][C:3]([N:13]2[C:25](=[O:24])[NH:27][NH:28][C:14]2=[O:15])=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 80519Methyl carbazateHCID 132729231-Chloro-5-fluoro-4-isocyanato-2-propoxybenzene

Product 1

HCID 13335302HCID 13335302, compoundYield 115.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-fluoro-4-chloro-5-n-propoxyphenyl isocyanate (1.8 g) in benzene (10 ml) was added to a toluene solution containing methoxycarbonylhydrazine (0.71 g), and the resultant mixture was allowed to stand overnight. The precipitated crystals were collected by filtration and dissolved in a 4M aqueous sodium hydroxide solution (10 ml) under heating. To the resulting solution, conc. hydrochloric acid was added, and the precipitated crystals were collected by filtration to give 2.6 g of 4-(4-chloro-2-fluoro-5-n-propoxyphenyl)urazol. M.P., 181°-182° C. IRνmax (cm-1): 3150, 1710, 1680. NMR δ (ppm): 1.1 (3H, t), 4.0 (3H, q), 7.0 (1H, d), 7.3 (1H, d).

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. dissolutiondissolved in a 4M aqueous sodium hydroxide solution (10 ml)
  3. temperatureunder heating
  4. additionTo the resulting solution, conc. hydrochloric acid was added
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-abf55d52f89d44e98d2fe5edde2e25c8
Source dataset
uspto-grants-1986_06
Patent number
US04593094

Reaction notes

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